Property
ActiveResidential
1/60
$2,250,000

2068 ROBERTS POINT DRIVE

Windermere, FL 34786
5
Beds
4
Baths
4,876
SqFt
1.04
Acres
STELLAR
#O6397543
Updated: Jun 1, 2026, 12:53pm

Property Description

One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita and Lake Access.

A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the property combines architectural presence, exceptional privacy, and resort-inspired living in a peaceful enclave known for estate-sized homes, mature landscaping, and private access to Lake Roberts.

Designed around a dramatic courtyard pool, the home creates a true indoor-outdoor lifestyle experience, ideal for both grand entertaining and everyday living. The detached guest casita is a standout feature, offering exceptional flexibility for guests, private office use, wellness retreat, creative studio, or evolving lifestyle needs.

Inside, soaring ceilings, polished marble tile flooring, detailed crown molding, and dramatic two-story living spaces create a sense of scale and elegance throughout. The thoughtfully updated chef’s kitchen is designed for gathering, featuring quartz countertops, an oversized island, premium KitchenAid and Bosch appliances, double ovens, wine refrigeration, and seamless connection to the expansive family room with custom built-ins and fireplace.

The private first-floor primary suite serves as a true retreat, offering direct courtyard and pool access, a spacious custom walk-in closet, and a beautifully appointed bath with dual vanities, jetted soaking tub, and walk-in shower. A second first-floor suite provides ideal accommodations for guests or family.

Upstairs, expansive, flexible living spaces include a large game room overlooking the courtyard, a dedicated office with custom built-ins, a private fitness room with balcony access, and additional secondary bedrooms thoughtfully arranged for privacy and functionality.

Outdoor living is equally compelling, with a screened resort-style saltwater pool and heated spa with waterfall, covered summer kitchen, multiple entertaining spaces, and the privacy that only a homesite of this scale can provide.

Waterford Pointe residents enjoy an exceptional lifestyle with private access to Lake Roberts, a waterfront clubhouse, tennis courts, playground, and beautifully tree-lined streets—all within one of Windermere’s most desirable gated communities.

Additional highlights include a 4-car garage, a new whole-house generator, three HVAC systems, a newly painted exterior courtyard, and highly regarded local schools.

For buyers seeking privacy, architectural character, flexible living, and established Windermere luxury—without the premium of direct lakefront pricing—this is a compelling opportunity.

**Private tours available by appointment**
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Included Appliances
Built-In OvenConvection OvenCooktopDishwasherDisposalElectric Water HeaterMicrowaveRange HoodRefrigeratorWater Filtration SystemWhole House R.O. SystemWine Refrigerator

Property Details

Highlights
View
Yes
Interior
Additional Rooms
Bonus RoomDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room SeparateInside UtilityInterior In-Law Suite w/Private EntryStorage Rooms
Appliances
Built-In OvenConvection OvenCooktopDishwasherDisposalElectric Water HeaterMicrowaveRange HoodRefrigeratorWater Filtration SystemWhole House R.O. SystemWine Refrigerator
Bathrooms Total Decimal
4
Building Area Total
8410
Cooling
Central AirZoned
Fireplace Features
ElectricFamily RoomNon Wood Burning
Flooring
Brick/StoneCarpetCeramic TileHardwood
Furnished
Unfurnished
Green Energy Efficient
Thermostat
Heating
ElectricHeat PumpZoned
Interior Features
Built-in FeaturesCathedral Ceiling(s)Ceiling Fan(s)Chair RailCrown MoldingDry BarEating Space In KitchenHigh CeilingsKitchen/Family Room ComboOpen FloorplanPrimary Bedroom Main FloorSplit BedroomStone CountersThermostatTray Ceiling(s)Walk-In Closet(s)
Laundry Features
Electric Dryer HookupLaundry Room
Living Area
4876
Other Equipment
Fuel Tank(s)GeneratorIrrigation Equipment
Rooms Total
15
Security Features
Gated CommunitySecurity GateSmoke Detector(s)
Virtually Staged
Yes
Window Features
BlindsShadesShutters
Construction
Architectural Style
CourtyardCustomFloridaOtherTraditional
Builder Name
CUSTOM
Building Area Source
Estimated
Building Area Units
Square Feet
Construction Materials
BlockStoneStucco
Direction Faces
East
Foundation Details
Slab
Levels
Two
Living Area Source
Public Records
Living Area Units
Square Feet
Property Condition
Completed
Roof
Tile
Stories Total
2
Year Built
1999
Site & Exterior
Additional Water Information
Private boat ramp for the community.
Covered Spaces
4
Exterior Features
BalconyCourtyardFire PitFrench DoorsIrrigation SystemLightingOutdoor GrillOutdoor KitchenPrivate EntrancePrivate MailboxRain GuttersSidewalk
Fencing
Other
Flood Zone Code
X
Garage Dimensions
21X44
Garage Spaces
4
Green Water Conservation
Low-Flow FixturesWhole House Water Purification
I D X Participation
Yes
Lot Features
LevelNear Golf CourseOversized LotSidewalk
Lot Size Acres
1.04
Lot Size Area
1.0373
Lot Size Dimensions
150 x 307
Lot Size Square Feet
45184
Lot Size Units
Acres
Number Of Wells
Yes
Open Parking
Yes
Other Structures
CabanaOther
Parking Features
BoatCircular DrivewayDrivewayGarage Door OpenerGarage Faces SideGolf Cart ParkingGuestParking Pad
Patio And Porch Features
CoveredEnclosedPatioScreenedSide Porch
Pool Features
Child Safety FenceGuniteHeatedIn GroundLightingOtherOutside Bath AccessSalt WaterScreen EnclosureSelf Cleaning
Public Survey Range
27
Public Survey Section
01
Road Frontage Type
Street PavedPrivate Road
Road Responsibility
Private Maintained Road
Road Surface Type
PavedAsphalt
Sewer
Septic Tank
Spa Features
HeatedIn Ground
Total Acreage
1 to less than 2
Utilities
Cable AvailableElectricity ConnectedPhone AvailablePropaneSprinkler WellStreet LightsUnderground UtilitiesWater Connected
Vegetation
Mature LandscapingOak TreesTrees/Landscaped
View
Trees/Woods
Water Access
Yes
Water Body Name
LAKE ROBERTS
Water Extras
Yes
Water Source
Public
Waterfront Features
LakeWaterfront
Zoning
R-CE
Financials
Association Fee
325
Association Fee Frequency
Monthly
Association Fee Includes
24-Hour GuardPrivate RoadRecreational Facilities
Calculated List Price By Calculated Sq Ft
461.44
Contract Status Change Date
2026-04-16
Current Price
2250000
Feed Types
BBO
Lease Considered
Yes
Minimum Lease
8-12 Months
Monthly H O A Amount
325
Ownership
Fee Simple
Parcel Number
012327911000560
Public Survey Township
23
Tax Annual Amount
12356.34
Tax Block
00
Tax Book Number
34-125
Tax Legal Description
WATERFORD POINTE PH 2 REPLAT 34/125 LOT56
Tax Lot
56
Tax Year
2025
Total Annual Fees
3900
Total Monthly Fees
325

Neighborhood & Lifestyle

Community & Association
Additional Lease Restrictions
The Buyer is to verify with the HOA and the Town of Windermere.
Association Amenities
ClubhouseFence RestrictionsGatedParkPlaygroundRecreation FacilitiesSecurityTennis Court(s)Vehicle Restrictions
Association Approval Required
Yes
Association Fee Requirement
Required
Association Name
Don Asher
Association Phone
407-425-4561
Community Features
Community Boat RampDockFishingLakeWater AccessWaterfrontClubhouseDeed RestrictionsGated Community - GuardGolf Carts OKNo Truck/RV/Motorcycle ParkingParkPlaygroundSidewalksTennis Court(s)
M L S Area Major
34786 - Windermere
Pet Restrictions
The Buyer is to verify with the HOA and the Town of Windermere.
Pets Allowed
Yes
Subdivision Name
WATERFORD POINTE PH 02 REP
Schools
Ratings
Elementary
Lake Whitney Elem
Middle
SunRidge Middle
High
West Orange High
Listing provided courtesy of STELLAR via IDX. Updated: Jun 1, 2026, 12:53pm.
David Dorman

Listing Agent

CENTURY 21 CARIOTI

Call Agent